Item: Apple iCloud
Rating: 8
Author: Jeff Eaton

Overall Satisfaction with Apple iCloud

Use Cases and Deployment Scope

Our org relies heavily on Dropbox for shared document collections, but most of the team members are Mac users, and iCloud's seamless file syncing between a single user's iOS MacOS devices has been a really useful addition to the mix. Most of us use iCloud to store and archive files created by compatible applications, then move things to Dropbox if they're "done" and need to be accessed by multiple team members.

In a few situations, we've used the collaborative authoring tools that Apple's free productivity apps provide (multiple users working on the same Keynote file in the leadup to a large meeting, for example).

Pros and Cons

Pros

Zero set up integration with Apple and many third-party apps.
MacOS and iOS document sharing is smooth to the point of being effortlessness.
Enough storage on the "free" tier that many team members can get by without an upgrade.

Cons

Weak to non-existent shared multi-user storage. i.e. "Here's a shared collection of presentations we all use".
Built-in iCloud support on an app-by-app basis is necessary to achieve "super seamless" workflow. Without that, it's just Apple's brand of a cloud-synced folder.

Return on Investment

Because the free-tier of iCloud is baked into MacOS and iOS, most of our team use it without even thinking about it. It solves the simplest case of cross-device syncing really well.
Trying to replace Dropbox with it is a no-go because of the incredibly limited collaboration features. If some future "Enterprise iCloud" tier with good multi-user support rolls out, it might be a better match.

Alternatives Considered

Dropbox, Dropbox Business and Box

iCloud is better than any competitors for single-user cross-machine file syncing on iOS and MacOS devices. It's passable for Windows machines but definitely not as well integrated into the OS.

For multi-user file sharing scenarios (putting all of a team's shared files in one place, for example), iCloud is too cumbersome to be useful.

Other Software Used

OmniGraffle

Performance

Occasionally, large files that haven't yet been synced require a few minutes to pull down but I've rarely noticed delays. It does a good job of keeping data cached on my local machines while updating them with changes from other machines transparently.

Usability

For the single-user scenarios, it's best at, iCloud's usability is great. For multi-user collaboration scenarios, though, it's still much more complicated than the competition.

Likelihood to Recommend

iCloud is at its best when a single user has multiple devices and uses the same apps on all or most of those devices. Keynote, Pages, IA Writer, MindNode, and other "fully integrated with iCloud" apps are great examples of how easy it can be.

It's less compelling when multiple users need a shared file repository — we just use Dropbox in that situation, and it's a good compliment.

It's also less valuable when the apps being used don't directly integrate with iCloud. The valuable cross-OS integration when switching from Mac to iOS and back is much clunkier in those situations. Kick the tires using the free iCloud features before depending too heavily on it.

Apple iCloud Feature Ratings

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iCloud: Fantastic cloud storage for a single user